methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose | 88390-62-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose
• 英文别名: methyl 4,6-O-benzylidene-2-O-methyl-α-D-ribo-hexopyranosid-3-ulose；methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-arabinohexopyranosid-3-ulose；(2R,4aR,6S,7R,8aR)-6,7-dimethoxy-2-phenyl-4a,6,7,8a-tetrahydro-4H-pyrano[3,2-d][1,3]dioxin-8-one
• CAS: 88390-62-9
• 化学式: C₁₅H₁₈O₆
• 分子量: 294.304
• InChiKey: WZULTIRVGOJYJD-LFHLZQBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以70%的产率得到methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-ribohexopyranosid-3-ulose
  参考文献：
  名称：

  New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

  摘要：

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.014
• 作为产物：
  描述：

  methyl 4,6-O-(R)-benzylidene-2-O-methyl-α-D-altropyranoside 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以68.3%的产率得到methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose
  参考文献：
  名称：

  The use of pyridinium chlorochromate for preparation of hexopyranosiduloses without epimerisation

  摘要：

  DOI：

  10.1016/s0008-6215(00)85688-8
• 作为试剂：
  描述：

  反式-1,2-二苯乙烯 在 Oxone 、 四丁基硫酸氢铵 、 edetate disodium 、 碳酸氢钠 、 methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以68%的产率得到Stilbene oxide
  参考文献：
  名称：

  New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

  摘要：

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.014

文献信息

• The use of pyridinium chlorochromate for preparation of hexopyranosiduloses without epimerisation
  作者：Brian B. Bissember、Richard H. Wightman

  DOI：10.1016/s0008-6215(00)85688-8

  日期：1980.5
• Complementary stereoselectivity in the reactions of hexopyranosid-4-uloses with methylmagnesium iodide and methyllithium
  作者：Juji Yoshimura、Ken-Ichi Sato

  DOI：10.1016/0008-6215(83)88491-2

  日期：1983.11
• New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars
  作者：José M. Vega-Pérez、Ignacio Periñán、Margarita Vega-Holm、Carlos Palo-Nieto、Fernando Iglesias-Guerra

  DOI：10.1016/j.tet.2011.07.014

  日期：2011.9

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.